The use of 1-amino-2-phenyl-1-cyclohexanecarboxylic acids as chiral auxiliaries in asymmetric Diels-Alder reactions.

被引：6

作者：

Avenoza, A

Cativiela, C

Paris, M

Peregrina, JM

机构：

[1] UNIV ZARAGOZA, INST CIENCIA MAT ARAGON, DEPT ORGAN CHEM, CSIC, E-50009 ZARAGOZA, SPAIN

[2] UNIV LA RIOJA, SECC CIENCIAS, EDIFICIO CIENT TECN, DEPT CHEM ORGAN CHEM, E-26001 LOGRONO, SPAIN

来源：

TETRAHEDRON | 1996年 / 52卷 / 13期

关键词：

D O I：

10.1016/0040-4020(96)00155-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This report describes the behavior of four 1-amino-2-phenyl-1-cyclohexanecarboxylic acids, obtained in enantiomerically pure form starting from asymmetric Diels-Alder reactions between 1,3-butadiene and chiral (E)-2-cyanocinnamates, as chiral auxiliaries in the asymmetric Diels-Alder reactions of cyclopentadiene with chiral methyl N-acryloyl-1-amino-2-phenyl-1-cyclohexanecarboxylates. A model based on the formation of an intramolecular hydrogen bond accounts for the stereochemical outcome in the catalyzed reactions.

引用

页码：4839 / 4848

页数：10

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